Synthesis of New Heterocyclic Fatty Compounds.

Fuermeier, S.; Metzger, Jürgen O.

doi:10.1002/chin.200325044

Cited by 3 publications

(4 citation statements)

References 10 publications

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“…Consequently, this reaction provides a route for the formation of long chain heterocyclic fatty acid derivatives in food products. Although heterocyclic fatty acid derivatives are not usually determined, their formation (or their syntheses) has been objective of diverse studies (see, for example, Fürmeier and Metzger, 2003;Gardner et al, 2000;Hidalgo and Zamora, 1995).…”

Section: Strecker Degradation Of Amino Acids Produced By Lipid Oxidatmentioning

confidence: 99%

Amino Acid Degradations Produced by Lipid Oxidation Products

Hidalgo

Zamora

2015

Critical Reviews in Food Science and Nutrition

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Differently to amino acid degradations produced by carbohydrate-derived reactive carbonyls, amino acid degradations produced by lipid oxidation products are lesser known in spite of being lipid oxidation a major source of reactive carbonyls in food. This article analyzes the conversion of amino acids into Strecker aldehydes, α-keto acids, and amines produced by lipid-derived free radicals and carbonyl compounds, as well as the role of lipid oxidation products on the reactions suffered by these compounds: the formation of Strecker aldehydes and other aldehydes from α-keto acids; the formation of Strecker aldehydes and olefins from amines; the formation of shorter aldehydes from Strecker aldehydes; and the addition reactions suffered by the olefins produced from the amines. The relationships among all these reactions and the effect of reaction conditions on them are discussed. This knowledge should contribute to better control food processing in order to favor the formation of desirable beneficial compounds and to inhibit the production of compounds with deleterious properties.

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Section: Strecker Degradation Of Amino Acids Produced By Lipid Oxidatmentioning

confidence: 99%

Amino Acid Degradations Produced by Lipid Oxidation Products

Hidalgo

Zamora

2015

Critical Reviews in Food Science and Nutrition

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“…Compounds 18-23 have greater pK a values than that of 1. The phenolic compounds (18 and 19), b-ketoester (20), ketone (21), amide (22) and alcohol (23) used in this study showed no inhibitory activity against pol a, pol b and TdT. These results Errors mean ± S.E.…”

Section: Enzymatic Inhibitory Activity Of Organic Acids Against Dna P...mentioning

confidence: 55%

“…Compounds 1, 2, 3, 5, 6, 13, 14, 15, 16, 17, 22, and 23 were obtained from commercial sources and used without further purification. Compounds 4, 18 7, 19 8, 20 9, 21 10, 22 12, 23 18, 24 19, 24 20 25 and 21 25 were prepared by literature procedures with slight modifications and characterized by NMR spectra. Compound 11 was prepared from the known compound 24 26 (Scheme 1).…”

Section: Organic Acidsmentioning

confidence: 99%

Chemical properties of fatty acid derivatives as inhibitors of DNA polymerases

Nakamura¹,

Takeuchi²,

Kuramochi³

et al. 2007

Org. Biomol. Chem.

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In this study, the chemical properties of organic acids as DNA polymerase inhibitors were examined. In total, we assayed the inhibitory activities of 23 compounds. We found that the DNA synthesis activity of DNA polymerase was usually reduced to less than 50% in the presence of 100 microM monoprotic acids, which have a Clog P value greater than 7.0 and a pK(a) value less than 5.4. With a minor modification these chemical properties applied to several organic fatty acids previously reported as DNA polymerase inhibitors. Moreover, we also examined the inhibitory activities of perfluorooctadecanoic acid (PFOdA) and perfluorooctanesulfonic acid (PFOS) against DNA polymerase beta in detail. These compounds inhibited the polymerase activity of pol beta competitively with template-primer DNA, and non-competitively with dNTPs. In addition, the 8 kDa domain-defective pol beta was also sensitive to these compounds. Our results suggest that the inhibitory mode of action of PFOdA and PFOS is different from that mediated by the classic fatty acid inhibitors against DNA polymerase beta.

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“…The oxidative cleavage of ozonides, epoxides and 1,2-diols has been intensively studied, [20][21][22][23][24][25][26] notably for the preparation of aldehydes, acids and esters. However, only very little attention has been devoted to fatty -hydroxyketones [27][28][29][30][31][32][33][34] and 1,2-diketones, [35][36][37] even though these compounds are usually proposed as reaction intermediates.…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic Cleavage of Fatty 1,2-Diketones to Esters

Chavallard

Miguel

et al. 2019

ACS Sustainable Chem. Eng.

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The cleavage of a fatty 1,2-diketone derived from methyl oleate into the corresponding esters, i.e., methyl nonanoate and dimethyl azelate was studied by organocatalysis using oxygen as a clean oxidant. Only carbene generated from thiazolium salts and K 2 CO 3 could efficiently catalyze this transformation. It was found that, under the optimized conditions, the oxidative cleavage leads to the formation of a 1:1 mixture of esters and potassium carboxylates.An acidic treatment of the mixture, followed by esterification with methanol, led to the desired 2 esters with 75 and 77% yield. This protocol was extended to a range of symmetrical and unsymmetrical fatty 1,2-diketones and the corresponding esters were isolated with 61-84% yield.

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Synthesis of New Heterocyclic Fatty Compounds.

Cited by 3 publications

References 10 publications

Amino Acid Degradations Produced by Lipid Oxidation Products

Amino Acid Degradations Produced by Lipid Oxidation Products

Chemical properties of fatty acid derivatives as inhibitors of DNA polymerases

Organocatalytic Cleavage of Fatty 1,2-Diketones to Esters

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